Halogen substituted dihydroxy diaryl methanes



Patented Mar. 9, 1954 2,671,813

UNITED STATES PATENT @FFICE HALOGEN SUBSTITUTED DIHYDROXY DIARYL METHANES Paul J. Stofiel, Florissant, MO., assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware N Drawing. Application November 2, 1951, Serial No. 254,659

6 Claims. (Cl. 260-619) This invention relates to a new and novel 1. Acompcund of the structure family of dihydroxy diaryl methanes. OH OH The new compounds may be represented by H1 the general formula 3- g 5 OH OH Hlg cni- Big B R where R is a hydrocarbon group and Hlg represents halogen. 2. A compound of the structure OH OH where R represents a hydrocarbon radical and 01 H,- 1 I-Ilg represents halogen and more particularly a chloro, bromo or iodo constituent adjacent the hydroxyl group. 'The position of the hydrocarbon group may vary and an additional halogen substituent may be present. Examples of suit- Where R 15 a branchedcham alkyl groupable hydrocarbon substituents comprise methyl, A compound of the structure ethyl, propyl, butyl, amyl, hexyl; octyl, decyl, 0H 0H cyclohexyl, methyl cyclohexyl, benzyl and phenyl C1 0 groups.

The new compounds were prepared by eliminating water of condensation by heating in the presence of an acidic condensation catalyst formaldehyde and the substituted phenol, the I reaction being terminated before resinous poly- CH3 CH3 mers are produced. The end point of the re- The thod of making a dihydroxy dlaryl action was determined by spot testing during methane Which Comprises eliminating water of the initial reaction. 1 ml. of the reaction mix condensation by hea in t p es ce of on was added t 3 1 of a Suitable pregipitant and acidic condensation catalyst formaldehyde and after crystal formation was noted, the reaction a 2-0111010 y disubstitllted P1181101 and mixture quenched by t addition of a mterminating the reaction before resinous polytant before resinous polymers were produced in riders are Produced amount sufficient to interfere with purification of h h d of ak a dihydroxy dlaryl the product. methane which comprises eliminating water of As one example of the preparation of the new condensation y h ating in the presence of an compounds, about 8 ml. of concentrated sulfuric acidic Condensation Catalyst formaldehyde and acid was added dropwise to a well-stirred solua zh d ha a ky su st tut d tion of 92.3 g. of 4-tert. butyl o-chlorophenol ph n l nd t rm at th a ti n b for (0.5 mole) and 7.5 g. trioxymethylene (0.25 mole) resinous polymers are producedin 50 ml. of glacial acetic acid. After the The method of making a Y Y diaryl exothermic reaction subsided the mixture was m than whi h mpr s s l m at Wat of heated at 95 C. for about 3 hours. Then 200 condensation by heating in the presence of an ml. of water were added and the mixture cooled acidic condensation catalyst formal y and to 30 c. The solids were filtered and washed bu y oeh1oro p ol a d inatin with cold water until free of acidity. The crude g tr before resinous polymers are P product was taken up in 200 ml. of benzene and following decolorization with charcoal, gave fine PAUL STOFFEL' white plates, M. P. 123.2-123.7 0., yield 51.5%.

Analysis of the product gave 6617,76 carbon, References Cited in the file of this patent 6.85% hydrogen and 18.85% chlorine. The UNITED STATES PATENTS values calculated for CziHzsClzoz are 66.12% b r Na Date carbon, 6.87% hydrogen and 18.62% chlorine. 1,707,181 W il r 1; ,1 Mar. 26, 1929 The new compolulds possess antiseptic and 2,544,826 Craige, Jr Mar. 13, 1951 germicidal properties and are also mild antioxidants. Although the invention has been 11- OTHER REFERENCES lustrated by reference to a particular example, it morestan Jour, Pharmacol, Exptl. Therapy,

will be appreciated that it is not limited thereto. vol. 96 (1949), pages 238-249 (12 pages). Page What is claimed is: an 241 only is relied on. 

1. A COMPOUND OF THE STRUCTURE 